A post on the The Beechwood Organization’s website announcing its homes at the Highlands Club in Aquebogue promises a “carefree, low-maintenance lifestyle” in a single-family home built by “Long Island’s leading residential builder.”

We all know the Long Island Expressway doesn’t lead to Greenport and Orient — this is actually a Route 58 sign — but what you might not know is that throughout the 1950s and 1960s many local officials hoped it would. (Credit: Grant Parpan photo illustration)

Driving to the end of the Long Island Expressway and exiting onto the western edge of Route 58, Riverhead’s commercial capital, it’s difficult to imagine that a plan once called for the island’s longest road to extend into Southold Town.

But drawn on a map titled “Expressway Plan 1959 County Planning Board” are two thick red lines that run from the Riverhead Town line to Old North Road in Orient. One line indicates eastbound Long Island Expressway traffic. The other shows traffic lanes heading west. (more…)